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US20030130348A1 - Polyunsaturated oil saponification - Google Patents

Polyunsaturated oil saponification Download PDF

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Publication number
US20030130348A1
US20030130348A1 US10/299,337 US29933702A US2003130348A1 US 20030130348 A1 US20030130348 A1 US 20030130348A1 US 29933702 A US29933702 A US 29933702A US 2003130348 A1 US2003130348 A1 US 2003130348A1
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US
United States
Prior art keywords
fatty acid
calcium salts
polyunsaturated
present
omega
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/299,337
Inventor
George Strohmaier
Eiler Frederiksen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to US10/299,337 priority Critical patent/US20030130348A1/en
Publication of US20030130348A1 publication Critical patent/US20030130348A1/en
Priority to US10/716,292 priority patent/US7098352B2/en
Priority to AU2003291054A priority patent/AU2003291054B8/en
Priority to EP03783640A priority patent/EP1585719A4/en
Priority to JP2004553871A priority patent/JP3917158B2/en
Priority to PCT/US2003/036821 priority patent/WO2004046086A1/en
Priority to MXPA05005316A priority patent/MXPA05005316A/en
Priority to ARP030104260A priority patent/AR042074A1/en
Priority to CA2506414A priority patent/CA2506414C/en
Priority to NZ540553A priority patent/NZ540553A/en
Priority to MYPI20034405A priority patent/MY138072A/en
Priority to US12/912,668 priority patent/US8093415B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/20—Inorganic substances, e.g. oligoelements
    • A23K20/24—Compounds of alkaline earth metals, e.g. magnesium
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids

Definitions

  • the present invention relates to the preparation of fatty acid calcium salts from high glyceride content polyunsaturated oils such as fish oils.
  • the fatty acid calcium salts are rich in desirable omega-3 fatty acids, including eicosapentanoic acid (EPA), decosahexanoic acid (DHA), decosapentanoic acid (DPA) and linolenic acid (LA).
  • EPA eicosapentanoic acid
  • DHA decosahexanoic acid
  • DPA decosapentanoic acid
  • LA linolenic acid
  • Omega-3 fatty acids are known to promote animal fertility, and have other nutritional and physiological properties as well.
  • the present invention therefore also relates to fatty acid calcium salts prepared by the method of the present invention high in desirable omega-3 fatty acids, and the use of these calcium salts as animal nutritional supplements.
  • the fatty acid calcium salts can be used to enrich the omega-3 fatty acid content of a variety of feed or food products, including pet food products.
  • Fatty acid calcium salts are known rumen-inert feed supplement for ruminants such as cattle. Fatty acids in calcium salt form are protected from microbial action in the rumen. Fatty acid calcium salt rumen bypass feed supplements are disclosed by U.S. Pat. Nos. 4,642,317; 4,826,694; 4,853,233 and 4,909,138. The disclosures of all four patents are incorporated herein by reference.
  • Polyunsaturated oils such as fish oils have glyceride contents as high as 100%. That is, all of the fatty acids can be in the glyceride form. Fatty acid glycerides do not readily react to form calcium salts using the processes disclosed by the above-listed patents. For a product to be commercially feasible, glyceride levels below about 5 weight percent are desirable to produce a free-flowing and stable product. The processes disclosed by the above-listed patents produce fatty acid calcium salts having much higher levels of unreacted glyceride. Products with residual glyceride contents above 5 weight percent lack storage stability, and are susceptible to oxidation, post-heating, melting, subsequent product solidification, and a tendency to form lumps upon storage.
  • U.S. patent application Ser. No. 09/990,784 discloses the preparation of fatty acid calcium salts from fatty acid feedstocks having glyceride contents as high as 60% by weight.
  • the disclosure of this application is incorporated herein by reference.
  • the process disclosed by this patent application can be used to prepare fatty acid calcium salts from polyunsaturated oils in general by diluting the glyceride content to about 60 weight percent or lower with a low glyceride content feedstock such as Palm Fatty Acid Distillate (PFAD). While the process disclosed by that patent application can be used to prepare fatty acid calcium salts rich in omega-3 fatty acids, there remains a need for fatty acid calcium salts having higher levels of omega-3 fatty acids.
  • PFAD Palm Fatty Acid Distillate
  • U.S. Pat. No. 6,229,031 discloses a high temperature saponification process for the preparation of fatty acid calcium salts from feedstocks containing glyceride contents as high as 100 weight percent. It has now been determined that this process can be used to prepare fatty acid calcium salts from polyunsaturated oils when omega-3 fatty acid levels are needed higher than that which can be prepared by the process disclosed by U.S. patent application Ser. No. 09/990,784. In particular, the high temperature process of U.S. Pat. No. 6,229,031 can be used to prepare fatty acid calcium stocks from feedstocks having glyceride contents greater than about 60 weight percent up to 100% glyceride content oils.
  • polyunsaturated oils are defined as having a glyceride content between about 60 and about 100 weight percent, preferably between about 70 and about 100 weight percent, more preferably between about 80 and about 100 weight percent, and even more preferably between about 90 and about 100 weight percent, with a glyceride content of 100% being most preferred.
  • the purpose of the present invention is to provide fatty acid calcium salts of polyunsaturated fatty acids from feedstocks for those acids that are typically very high in glyceride content, without have to significantly dilute the feedstock, if at all, with low glyceride content feedstocks that contain little, if any, polyunsaturated fatty acids.
  • any polyunsaturated oil containing useful levels of polyunsaturated fatty acids is suitable for use with the present invention, and for purposes of the present invention is included within the definition of a polyunsaturated oil.
  • an oil with a glyceride content between 60 and 100 weight percent has utility as a polyunsaturated oil, it is within the definition of high glyceride content polyunsaturated oils for purposes of the present invention.
  • the present invention is advantageously used with polyunsaturated oils having a low level of polyunsaturated fatty acids because with the present invention the polyunsaturated fatty acid concentration is essentially conserved.
  • Calcium salts of polyunsaturated oils containing between about 3 and about 100 weight percent unsaturated fatty acids based on the total fatty acid content can be formed using the methods of the present invention. Oils with lower levels of polyunsaturated fatty acids may be used if they have utility based on their polyunsaturated fatty acid content.
  • U.S. Pat. No. 6,229,031 can be used to prepare fatty acid calcium salts from pure polyunsaturated oils such as fish oils, and from polyunsaturated oils that have been diluted with lower glyceride content feedstocks such as PFAD down to glyceride contents as low as about 60 weight percent.
  • the disclosure of U.S. Pat. No. 6,229,031 is also incorporated herein by reference.
  • any polyunsaturated oil of animal, vegetable or fish origin including those disclosed in the above-referenced U.S. patent application Ser. No. 09/990,784 can be used with the present invention, either in pure form or diluted to lower the glyceride content.
  • suitable oils include soybean oil, cottonseed oil, flax seed oil, rape seed oil, and the like.
  • U.S. Pat. No. 6,299,031 can be used to prepare fatty acid calcium salts from fish oil sources such as menhaden, herring, mackerel, caplin, tilapia, tuna, sardine, pacific saury, krill, and the like, as well as from polyunsaturated oils other that fish oils.
  • the fatty acid calcium salts include calcium salts containing from about 1 to about 20% by weight of DHA, and/or from about 1 to about 20% by weight of EPA, and/or from about 1 to about 20% by weight of DPA, and/or from about 1 to about 20% by weight of LA.
  • Other conventional biologically active ingredients can be added to the calcium salt products at conventional levels by known means.
  • the polyunsaturated oils can be unstable if over-processed under the saponification conditions disclosed by U.S. pat. No. 6,299,031.
  • Preferred methods according to the present invention hold the polyunsaturated oil at ambient or below ambient temperature conditions, more preferably between about 10 and about 30 degrees C.
  • Preferred methods also additionally blanketing the headspace with mixtures of inert gases to eliminate oxygen. It is also preferred to blend an effective amount of one or more antioxidants and chelating agents for polyunsaturated oils into the admixture to be reacted.
  • the preferred reaction temperature is between about 150 and about 250 degrees C., and the preferred reation time within this temperature range is between about 2 and about 30 minutes.
  • a preferred step for maintaining product stability is to run the reaction at either reduced pressures, vacuum conditions, or in the presence of an inert gas mixture such as N 2 or CO 2 or other. This will prevent the oxidation at the elevated temperatures that will destabilize the polyunsaturated fatty acids in calcium salt form.
  • Another preferred step for maintaining stability is to immediately cool the product as quickly as possibly while simultaneously flaking the material into a free flowing granular product with minimal fines.
  • the calcium salts of the present invention can be used as rumen-inert feed supplements for ruminants such as cattle, the calcium salts are also useful in general as nutritional supplement for humans, other mammals, and non-mammals, including birds and fish.
  • methods in accordance with the present invention add an effective amount of the fatty acid calcium salts of the present invention to a food product including pet food products such as cat food and dog food.
  • Effective amounts include amounts that will provide a food product having an omega-3 fatty acid content between about 0.05 and about 1.5 weight percent. Omega-3 fatty acid content between about 0.1 weight percent and about 0.5 weight percent are preferred.
  • the present invention also includes food products containing the fatty acid calcium salts of the present invention within the ranges described, including pet food products such as cat food and dog food.
  • the cat foods and dog foods include dry, semi-moist and moist cat food and dog food prepared by otherwise conventional methods from conventional formulations incorporating conventional pet food ingredients.
  • the fatty acid calcium salts of the present invention can be used in the fertility enhancement methods disclosed by WO 99/66877, which is incorporated herein by reference.
  • the present invention therefore includes methods according to that publication using the calcium salts of the present invention.
  • the present invention thus provides a means by which omega-3 fatty acid rich calcium salts may be prepared having utility as nutritional supplements for essentially any animal for which omega-3 fatty acids provide nutritional or therapeutic benefit.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Birds (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Fodder In General (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Free-flowing fatty acid calcium salt products are discclosed containing at least one omega-3 fatty acid selected from DHA, EPA, DPA and LA, wherein each fatty acid, when present, is at a level between about 1 and about 25% by weight. The preparation of fatty acid calcium salts from high glyceride content polyunsaturated oils by saponification processes is also disclosed.

Description

    CROSS-REFERENCE TO RELATED APPLICATION
  • The present application claims priority benefit of U.S. Provisional Patent Application Serial No. 60/334,471 filed Nov. 16, 2001, the disclosure of which is incorporated by reference.[0001]
    • BACKGROUND
  • The present invention relates to the preparation of fatty acid calcium salts from high glyceride content polyunsaturated oils such as fish oils. The fatty acid calcium salts are rich in desirable omega-3 fatty acids, including eicosapentanoic acid (EPA), decosahexanoic acid (DHA), decosapentanoic acid (DPA) and linolenic acid (LA). [0002]
  • Omega-3 fatty acids are known to promote animal fertility, and have other nutritional and physiological properties as well. The present invention therefore also relates to fatty acid calcium salts prepared by the method of the present invention high in desirable omega-3 fatty acids, and the use of these calcium salts as animal nutritional supplements. The fatty acid calcium salts can be used to enrich the omega-3 fatty acid content of a variety of feed or food products, including pet food products. [0003]
  • The enrichment of food products with omega-3 fatty acids has proven to be problematic. The addition of polyunsaturated oils to certain feed or food products to enhance their omega-3 fatty acid content produces an unacceptable yield loss in the levels of the omega-3 fatty acids desired. This is proven to particularly be a problem with enriching the omega-3 fatty acid content of pet foods. [0004]
  • Fatty acid calcium salts are known rumen-inert feed supplement for ruminants such as cattle. Fatty acids in calcium salt form are protected from microbial action in the rumen. Fatty acid calcium salt rumen bypass feed supplements are disclosed by U.S. Pat. Nos. 4,642,317; 4,826,694; 4,853,233 and 4,909,138. The disclosures of all four patents are incorporated herein by reference.[0005]
    • DESCRIPTION OF THE INVENTION
  • It has now been discovered that the omega-3 fatty acid yield loss is solved by converting the pure polyunsaturated oils to fatty acid calcium salts and using these calcium salts instead as the nutritional supplements. However, it is not commercially feasible to use the processes disclosed by the above-listed patents to prepare fatty acid calcium salts from polyunsaturated oils because of their high glyceride content. [0006]
  • Polyunsaturated oils such as fish oils have glyceride contents as high as 100%. That is, all of the fatty acids can be in the glyceride form. Fatty acid glycerides do not readily react to form calcium salts using the processes disclosed by the above-listed patents. For a product to be commercially feasible, glyceride levels below about 5 weight percent are desirable to produce a free-flowing and stable product. The processes disclosed by the above-listed patents produce fatty acid calcium salts having much higher levels of unreacted glyceride. Products with residual glyceride contents above 5 weight percent lack storage stability, and are susceptible to oxidation, post-heating, melting, subsequent product solidification, and a tendency to form lumps upon storage. [0007]
  • U.S. patent application Ser. No. 09/990,784 discloses the preparation of fatty acid calcium salts from fatty acid feedstocks having glyceride contents as high as 60% by weight. The disclosure of this application is incorporated herein by reference. The process disclosed by this patent application can be used to prepare fatty acid calcium salts from polyunsaturated oils in general by diluting the glyceride content to about 60 weight percent or lower with a low glyceride content feedstock such as Palm Fatty Acid Distillate (PFAD). While the process disclosed by that patent application can be used to prepare fatty acid calcium salts rich in omega-3 fatty acids, there remains a need for fatty acid calcium salts having higher levels of omega-3 fatty acids. [0008]
  • U.S. Pat. No. 6,229,031 discloses a high temperature saponification process for the preparation of fatty acid calcium salts from feedstocks containing glyceride contents as high as 100 weight percent. It has now been determined that this process can be used to prepare fatty acid calcium salts from polyunsaturated oils when omega-3 fatty acid levels are needed higher than that which can be prepared by the process disclosed by U.S. patent application Ser. No. 09/990,784. In particular, the high temperature process of U.S. Pat. No. 6,229,031 can be used to prepare fatty acid calcium stocks from feedstocks having glyceride contents greater than about 60 weight percent up to 100% glyceride content oils. Therefore, for purposes of the present invention polyunsaturated oils are defined as having a glyceride content between about 60 and about 100 weight percent, preferably between about 70 and about 100 weight percent, more preferably between about 80 and about 100 weight percent, and even more preferably between about 90 and about 100 weight percent, with a glyceride content of 100% being most preferred. [0009]
  • The purpose of the present invention is to provide fatty acid calcium salts of polyunsaturated fatty acids from feedstocks for those acids that are typically very high in glyceride content, without have to significantly dilute the feedstock, if at all, with low glyceride content feedstocks that contain little, if any, polyunsaturated fatty acids. Thus essentially any polyunsaturated oil containing useful levels of polyunsaturated fatty acids is suitable for use with the present invention, and for purposes of the present invention is included within the definition of a polyunsaturated oil. Stated another way, if an oil with a glyceride content between 60 and 100 weight percent has utility as a polyunsaturated oil, it is within the definition of high glyceride content polyunsaturated oils for purposes of the present invention. [0010]
  • The present invention is advantageously used with polyunsaturated oils having a low level of polyunsaturated fatty acids because with the present invention the polyunsaturated fatty acid concentration is essentially conserved. Calcium salts of polyunsaturated oils containing between about 3 and about 100 weight percent unsaturated fatty acids based on the total fatty acid content can be formed using the methods of the present invention. Oils with lower levels of polyunsaturated fatty acids may be used if they have utility based on their polyunsaturated fatty acid content. [0011]
  • Thus, the process of U.S. Pat. No. 6,229,031 can be used to prepare fatty acid calcium salts from pure polyunsaturated oils such as fish oils, and from polyunsaturated oils that have been diluted with lower glyceride content feedstocks such as PFAD down to glyceride contents as low as about 60 weight percent. The disclosure of U.S. Pat. No. 6,229,031 is also incorporated herein by reference. Essentially any polyunsaturated oil of animal, vegetable or fish origin, including those disclosed in the above-referenced U.S. patent application Ser. No. 09/990,784 can be used with the present invention, either in pure form or diluted to lower the glyceride content. Examples of suitable oils include soybean oil, cottonseed oil, flax seed oil, rape seed oil, and the like. [0012]
  • Accordingly, the process of U.S. Pat. No. 6,299,031 can be used to prepare fatty acid calcium salts from fish oil sources such as menhaden, herring, mackerel, caplin, tilapia, tuna, sardine, pacific saury, krill, and the like, as well as from polyunsaturated oils other that fish oils. The fatty acid calcium salts include calcium salts containing from about 1 to about 20% by weight of DHA, and/or from about 1 to about 20% by weight of EPA, and/or from about 1 to about 20% by weight of DPA, and/or from about 1 to about 20% by weight of LA. Other conventional biologically active ingredients can be added to the calcium salt products at conventional levels by known means. [0013]
  • The polyunsaturated oils can be unstable if over-processed under the saponification conditions disclosed by U.S. pat. No. 6,299,031. Preferred methods according to the present invention hold the polyunsaturated oil at ambient or below ambient temperature conditions, more preferably between about 10 and about 30 degrees C. Preferred methods also additionally blanketing the headspace with mixtures of inert gases to eliminate oxygen. It is also preferred to blend an effective amount of one or more antioxidants and chelating agents for polyunsaturated oils into the admixture to be reacted. [0014]
  • It is also preferable to preheat the admixture in an appropriate heat exchange device immediately prior to the high temperature reactor, and also to blend the admixture with metallic rare earth metal oxides or their hydrated forms. Stability of the calcium salts can also be improved by limiting the reaction time and temperature. The preferred reaction temperature is between about 150 and about 250 degrees C., and the preferred reation time within this temperature range is between about 2 and about 30 minutes. [0015]
  • A preferred step for maintaining product stability is to run the reaction at either reduced pressures, vacuum conditions, or in the presence of an inert gas mixture such as N[0016] 2 or CO2 or other. This will prevent the oxidation at the elevated temperatures that will destabilize the polyunsaturated fatty acids in calcium salt form. Another preferred step for maintaining stability is to immediately cool the product as quickly as possibly while simultaneously flaking the material into a free flowing granular product with minimal fines.
  • While the calcium salts of the present invention can be used as rumen-inert feed supplements for ruminants such as cattle, the calcium salts are also useful in general as nutritional supplement for humans, other mammals, and non-mammals, including birds and fish. [0017]
  • Thus, methods in accordance with the present invention add an effective amount of the fatty acid calcium salts of the present invention to a food product including pet food products such as cat food and dog food. Effective amounts include amounts that will provide a food product having an omega-3 fatty acid content between about 0.05 and about 1.5 weight percent. Omega-3 fatty acid content between about 0.1 weight percent and about 0.5 weight percent are preferred. The present invention also includes food products containing the fatty acid calcium salts of the present invention within the ranges described, including pet food products such as cat food and dog food. The cat foods and dog foods include dry, semi-moist and moist cat food and dog food prepared by otherwise conventional methods from conventional formulations incorporating conventional pet food ingredients. [0018]
  • The fatty acid calcium salts of the present invention can be used in the fertility enhancement methods disclosed by WO 99/66877, which is incorporated herein by reference. The present invention therefore includes methods according to that publication using the calcium salts of the present invention. [0019]
  • The present invention thus provides a means by which omega-3 fatty acid rich calcium salts may be prepared having utility as nutritional supplements for essentially any animal for which omega-3 fatty acids provide nutritional or therapeutic benefit. [0020]

Claims (1)

What is claimed is:
1. A free-flowing fatty acid calcium salt product comprising at least one omega-3 fatty acid selected from the group consisting of DHA, EPA, DPA and LA, wherein each fatty acid, when present, is at a level between about 1 and about 25% by weight
US10/299,337 2001-11-16 2002-11-18 Polyunsaturated oil saponification Abandoned US20030130348A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
US10/299,337 US20030130348A1 (en) 2001-11-16 2002-11-18 Polyunsaturated oil saponification
MYPI20034405A MY138072A (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils
JP2004553871A JP3917158B2 (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oil
AU2003291054A AU2003291054B8 (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils
EP03783640A EP1585719A4 (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils
US10/716,292 US7098352B2 (en) 2001-11-16 2003-11-18 Calcium salt saponification of polyunsaturated oils
PCT/US2003/036821 WO2004046086A1 (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils
MXPA05005316A MXPA05005316A (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils.
ARP030104260A AR042074A1 (en) 2002-11-18 2003-11-18 PREPARATION OF CALCIUM SALTS OF POLYINSATURED OILS BY SAPONIFICATION OF MARINE ANIMAL OILS
CA2506414A CA2506414C (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils
NZ540553A NZ540553A (en) 2002-11-18 2003-11-18 Calcium salt saponification of polyunsaturated oils
US12/912,668 US8093415B2 (en) 2001-11-16 2010-10-26 Polyunsaturated fatty acid monovalent and divalent metal salt synthesis

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33447101P 2001-11-16 2001-11-16
US10/299,337 US20030130348A1 (en) 2001-11-16 2002-11-18 Polyunsaturated oil saponification

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/716,292 Continuation-In-Part US7098352B2 (en) 2001-11-16 2003-11-18 Calcium salt saponification of polyunsaturated oils

Publications (1)

Publication Number Publication Date
US20030130348A1 true US20030130348A1 (en) 2003-07-10

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US10/299,337 Abandoned US20030130348A1 (en) 2001-11-16 2002-11-18 Polyunsaturated oil saponification

Country Status (10)

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US (1) US20030130348A1 (en)
EP (1) EP1585719A4 (en)
JP (1) JP3917158B2 (en)
AR (1) AR042074A1 (en)
AU (1) AU2003291054B8 (en)
CA (1) CA2506414C (en)
MX (1) MXPA05005316A (en)
MY (1) MY138072A (en)
NZ (1) NZ540553A (en)
WO (1) WO2004046086A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
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US20060045957A1 (en) * 2004-08-27 2006-03-02 Archer-Daniels-Midland Company High-fat animal feed pellets and method for making same
EP1585719A4 (en) * 2002-11-18 2007-02-21 Virtus Nutrition Llc Calcium salt saponification of polyunsaturated oils
WO2007066232A3 (en) * 2005-10-07 2007-11-01 Ocean Nutrition Canada Ltd Salts of fatty acids and methods of making and using thereof
US8178707B2 (en) 2010-03-25 2012-05-15 Jost Chemical Company Co-precipitated salts of fatty acids
CN108892610A (en) * 2018-04-30 2018-11-27 石河子大学 A kind of preparation method of feeding fatty acid calcium
US10653703B2 (en) * 2015-09-03 2020-05-19 Solutex Na Llc Compositions comprising omega-3 fatty acids, 17-HDHA and 18-HEPE and methods of using same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1983041A4 (en) * 2005-12-30 2010-09-22 Norel S A Method for producing calcium soaps for animal feed
US8203013B2 (en) * 2007-08-31 2012-06-19 Jh Biotech, Inc. Preparation of fatty acids in solid form

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IE50028B1 (en) * 1979-12-19 1986-02-05 Tate & Lyle Plc Process for the production of a surfactant containing sucrose esters
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EP1585719A4 (en) * 2002-11-18 2007-02-21 Virtus Nutrition Llc Calcium salt saponification of polyunsaturated oils
US20060045957A1 (en) * 2004-08-27 2006-03-02 Archer-Daniels-Midland Company High-fat animal feed pellets and method for making same
US8137719B2 (en) 2004-08-27 2012-03-20 Adm Alliance Nutrition, Inc. High-fat animal feed pellets and method for making same
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US8178707B2 (en) 2010-03-25 2012-05-15 Jost Chemical Company Co-precipitated salts of fatty acids
US10653703B2 (en) * 2015-09-03 2020-05-19 Solutex Na Llc Compositions comprising omega-3 fatty acids, 17-HDHA and 18-HEPE and methods of using same
CN108892610A (en) * 2018-04-30 2018-11-27 石河子大学 A kind of preparation method of feeding fatty acid calcium

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EP1585719A4 (en) 2007-02-21
CA2506414C (en) 2011-09-20
AU2003291054A1 (en) 2004-06-15
AR042074A1 (en) 2005-06-08
JP2006517239A (en) 2006-07-20
EP1585719A1 (en) 2005-10-19
JP3917158B2 (en) 2007-05-23
WO2004046086A1 (en) 2004-06-03
MXPA05005316A (en) 2005-11-17
MY138072A (en) 2009-04-30
AU2003291054B8 (en) 2009-01-22
NZ540553A (en) 2008-02-29
AU2003291054B2 (en) 2008-12-18

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